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. Author manuscript; available in PMC: 2018 Sep 1.
Published in final edited form as: Bioorg Med Chem. 2017 Jul 20;25(17):4845–4854. doi: 10.1016/j.bmc.2017.07.035

Scheme 2.

Scheme 2

Synthesis of 5-O-alkyl-2,3-dehydrosilybins (29–35). Reactants and conditions: i) (a) BnBr (1.1 eq), K2CO3 (4 eq), acetone (0.1 M), argon, reflux overnight; (b) Remove acetone, DMF (0.25 M), BnBr (2.2 eq), K2CO3 (3 eq), rt, 4 h, air; ii) (a) RI or RBr (8 eq), K2CO3 (8 eq), DMF (0.2 M), rt, 4 h; (b) ammonium formate (10 eq), EtOAc and MeOH, Pd/C (20%), reflux, overnight, argon.